HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 19002927, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 2-Iodo-6-methylpyridin-3-ol | HCID 89957 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 19002927 | HCID 19002927 | 86% |
Reaction Steps
A mixture of 2-iodo-6-methylpyridine-3-ol (20 g, 85 mmol), CuI (2.1 g, 11 mmol), trimethylsilyl acetylene (23.4 g. 238 mmol) and bis(triphenylphosphine)palladium(II)chloride (5.37 g, 7.65 mmol) in Et3N (380 mL) was heated to reflux for 20 hr. The mixture was cooled and diluted with ether and filtered through celite. The flitrate was concentrated in vacuo and the residue was chromatographed on silica gel (eluted with 10% EtOAc in hexane) to give 15 g (86% ) of the title compound. 1H NMR (CD3COCD3) δ 0.40 (9H, s), 2.54 (3H, s), 7.12 (1H, d, J=8 Hz), 7.14 (1H, s), 7.75 (1H, d, J=8 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05374635 |
| Source dataset | uspto-grants-1994_12 |
| ORD ID | ord-e6aa420505a04c74ac6c0c1acd4a72ac |
| Source note | uspto-grants-1994_12 |